It costs about $2000 in Destin, FL for instance to convert a regular residential use to STR use permit if it's the first time the house being coverted for usage.

I do have a handful of clients that have ended up using multiple CPAs just due to who their partners were on different deals, and even in those cases they almost always end up consolidating to a single CPA - taxes are enough of a headache without dealing with 3 different professionals who each only have a slice of the whole picture.If you are going to regularly be investing across the country, it doesn't hurt to work with a firm that has State and Local Tax (often referred to as "SALT") internal resources, though typically this does come from larger firms with larger fees. 

The owner I know uses a local handyman service they've built a relationship with to handle one-off issues that come up and perform regular maintenance, and it sounds like you've already got cleaning locked down. 

You can definitely start with a regular conventional loan for your investment property and then buy a primary after. 

The umbrella policy also covers things not included in a regular landlord liability policy.

He's is the only member of the HOA.Two units are being rented out as regular annual rentals.Rest are medium term rentals (90 day) for a local hospital.Sp would that mean you can turn it into an apartment building?  

Hi Jason,They are available, but a regular cash out may be a better option depending on the use of the funds (short-term or long-term).

Fish and camping have also always been a regular pass time.

But I’m wondering—do property managers who aren’t in the office regularly find value in these kinds of insights?

You need to find a regular local lender who can tell you what you will need which will be 20-30 percent depending on the rate you are after.But, the easiest way for flippers to become owners is to hold every 4th property you flip and rent it at high rent since it's a full renovation.